The Best Holiday Activities in Chicago

Not only is it November, but it’s also dipped down into the 30s here in Chicago. Sooo…. if it’s basically winter now, I think that justifies a little holiday cheer, right? And while I’m not quite ready to pump the Christmas jams, I am starting to get excited about all of the fun holiday activities in Chicago?

Best Holiday Activities in Chicago

1. Christkindlmarket

The Christkindlmarket is one of the most beloved Christmas traditions in Chicago. Even when it’s cold, this outdoor market is packed with people shopping around and hoping to get their hands on a pretzel or mug of hot spiced wine. (YUM!) If you’ve never been, you definitely have to add it to your list!

2. Zoo Lights

Going to Zoo Lights is one of my personal favorite holiday activities. It’s pretty magical to walk around Lincoln Park Zoo completely decorated in lights. There’s even holiday music playing wherever you go! Grab your significant other, some friends or your family, take a stroll around, and then grab dinner in Lincoln Park. The perfect evening!

3. Ice Skating

If you go to Millennium Park, there are two ice skating options. The first is a rink right by the bean, which is super fun – especially if you have out of towners with you. If you’re a little more advanced, you could also skate on the Maggie Daley “Ribbon.” The path, which is twice a long as a traditional skating rink, winds through the park and is really pretty when there’s snow on the trees! You can get information about both on this site.

4. Visit the big Christmas trees!

Every year I love to visit three Christmas trees in the city. The first one is inside 900 North Michigan. There’s something about doing your Christmas shopping with a huge tree in the middle of the building – it’s the best! My other favorite is just a few blocks away, outside of the Waldorf Astoria Hotel. That hotel is pretty glamorous on it’s own, but a big beautiful Christmas tree makes it even better. And the last is outside of The Wrigley Building, pictured at the top of this post. Swoon.

5. See A Christmas Carol at The Goodman

Get this. The Goodman Theatre has been performing A Christmas Carol to Chicago audiences for 40 YEARS. Seriously, how amazing is that?! If you’ve only ever seen movie versions, I’d definitely grab some tickets to the live production. It will give you all the Christmas feels!

6. Walk past Macy’s Windows

If you are a true Chicagoan, these will always be “the Marshall Field’s windows” – but either way, Macy’s still does a beautiful job. And after you check out the themed window displays, you can continue down State Street to see their wreaths and horns and crazy amounts of lights. So festive!

7. Christmas Around the World at The Museum of Science and Industry

I’ll be honest, I’ve never done this… but after doing some research, I totally want to now! Christmas Around the World at The Museum of Science and Industry features a four story floor-to-dome Grand Tree – and if that wasn’t enough, there are 50 more trees and displays all around it representing different holiday traditions from cultures all over the world. SO INTO THIS.
Also, one of my readers (thanks Tiffany!) told me about an adults-only party on November 17th, if you want to check this out while sipping holiday cocktails. How fun is that? You can get more info about MSI After Hours: Naughty or Nicehere.

8. Holiday Tea at The Drake

So you wanna be fancy, huh? Then you better go to the Winter Wonderland Afternoon Tea at The Drake. Bring your favorite ladies and sip on French tea and pastries while listening to Christmas Carolers and a harpist!

9. Go see The Nutcracker

Nobody does The Nutcracker like the The Joffrey Ballet. But last year, they reinvented the classic production with the help of Tony Award winning director, Christopher Wheeldon. It’s been described as “a must see tradition boldly reinvented for a new generation.” Intrigued? Me too!

10. Ride the Holiday Train

I know this requires a little luck… but if the Holiday Train pulls up, your commute just got WAY more fun!

So Chicago is my favourite city that I’ve never visited! If that even makes any sense! It’s on top of my list and where I plan to be for my 40th when it rolls around. I have always loved everything I’ve seen and heard about it and now I have my fav blogger Chicagoians making me even more excited to visit. This list sounds like so much fun!

There is actually a CTA schedule that gives you the times/which days the different lines will be doing the holiday train & there are actually holiday buses with Santa, too! My friend was in from out of town last year & so I stalked the site to make sure she got the full Chicago Christmas experience!

Primary Sidebar

Welcome to Lake Shore Lady!

Oh, hey! My name is Lauren, and this blog is all about living your happiest and healthiest life. Love style? Cooking? Fitness? Chicago? If any answer is yes, I hope you'll stay a while! Learn more about Lauren